Image credit: Masyn Winn (Photo by Bill Mitchell)
When the Cardinals selected Masyn Winn with their second-round pick, they announced him as a shortstop/righthander. Even in a time where pro teams have been more willing to entertain the idea of two-way players, Winn’s status as a high school-to-pro two-way player is quite rare.
Most of the two-way players in recent years (Brendan McKay, Tanner Dodson, Jared Walsh and Jake Cronenworth) are college players who did both at the Division I level and then carried that versatility over to pro ball.
But Winn isn’t unique. In the 2008 draft, the Red Sox took Casey Kelly in the first round. Kelly was a two-way star in high school who was also a high school quarterback. He had signed to play football at Tennessee, but Boston induced him to give up football with a $3 million signing bonus.
They also told Kelly that he could both pitch and hit. It’s likely instructive for how the Cardinals will try to develop Winn. A two-way outfielder/pitcher or first baseman/pitcher can slip back and forth with days of rest between pitching outings without worrying too much about blowing out his arm. But a shortstop has to make many more high-effort throws, making it very difficult to slip back and forth between the two positions.
The Red Sox divided Kelly’s season into two halves. In the first half, Kelly pitched. And then in July, he switched to playing shortstop. By doing so, he never had the added wear and tear of doing both at the same time.
In his pro debut, the Red Sox let Kelly focus entirely on being a position player as he got 130 at-bats as a shortstop with the club’s Rookie-level Gulf Coast League team and short-season Lowell.
But in 2009, the Red Sox let him do both. He went out in April as a pitcher for low Class A Greenville. He made 17 starts and threw 95 innings between there and high Class A Salem before hopping off the mound with a final start on July 7. Then after a week break, he began DHing on July 14 and moved to shortstop for the first time on July 19. He spent the second half as an everyday shortstop, compiling 162 at-bats.
For Kelly, that back and forth proved to be a one-year experiment. Most scouts had preferred Kelly as a pitcher, but he liked to hit. He hit .222/.302/.340 in 2009 while going 7-5, 2.08 on the mound. Kelly switched to being a full-time pitcher in 2010. He never played another game at shortstop, and has had a long career but only made 46 appearances over parts of four seasons in the majors.